

Structures and Photoluminescent Properties of Two Complexes Based on Dipyrido[3,2-a: 2',3'-c]phenazine and 2,4'-Biphenyldicarboxylic Acid①
English
Structures and Photoluminescent Properties of Two Complexes Based on Dipyrido[3,2-a: 2',3'-c]phenazine and 2,4'-Biphenyldicarboxylic Acid①
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1 INTRODUCTION
The keen interest in the design and synthesis of complexes stems not only from their interesting structural diversity but also from their potential applications in functional materials[1-8]. However, the construction of complexes with targeted architectures and predictable properties remains a farreaching challenge, since there are multifarious factors influencing the construction. In this context, the careful selection of multifunctional ligands and metal ions can be beneficial to fabricate desired complexes. The mono- and multidentate N-donor ligands, such as pyridine[9], imidazole[10], tetrazole[11], and 1, 10-phenanthroline (phen)[12, 13] as good candidates for the construction of coordination complexes, have aroused a good deal of interest from chemists. Among such work, phen and its derivatives are good candidates for the construction of MOFs with novel architectures because these ligands exhibit excellent coordinating capacities and potential supramolecular recognition sites for π-π aromatic stacking interactions[14-17]. We have been interested in constructing new Cd (II) and Zn (II) complexes with phen derivatives, and two complexes [Cd (2, 4′-bpdc)(DPPZ)]2n·nH2O (1) and [Zn (2, 4′-Hbpdc)2(DPPZ)]·H2O (2) (DPPZ = dipyrido[3, 2-a:2′, 3′-c]phenazine, 2, 4′-H2bpdc = 2, 4′-biphenyldicarboxylic acid) have been isolated. The structures and photoluminescent properties of the title complexes are investigated in detail.
2 EXPERIMENTAL
2.1 Materials and instruments
DPPZ ligand was synthesized according to the literature method[18] and all other chemicals were of analytical grade and used as received. Elemental analysis was recorded on a Perkin-Elmer 240C elemental analyzer. IR spectra were recorded within the 4000 ~ 400 cm-1 region on a Perkin-Elmer 2400LSII spectrometer. Powder X-ray diffraction (XRD) was measured on a D/MAX-3C diffractometer with CuKa radiation (λ = 0.15406 nm) at room temperature. The solid-state photoluminescent spectrum was taken on a Perkin-Elmer LS55 spectrometer.
2.2 Syntheses of complexes 1 and 2
CdSO4·8/3H2O (0.0513 g, 0.2 mmol), DPPZ (0.0565 g, 0.2 mmol), 2, 4′-H2bpdc (0.0484 g, 0.2 mmol) and NaOH (0.016 g, 0.40 mmol) were dissolved in distilled water (15 mL), and the resulting solution was stirred for about 1 h at room temperature, sealed in a 25 mL Teflon-lined stainless-steel autoclave and heated at 433 K for 3 d under autogenous pressure. Upon cooling and opening the bomb, yellow block crystals of 1 were collected with a yield of 52% (based on Cd) by filtration and washed with water and ethanol for several times. Anal. Calcd. (%) for 1: C, 59.69; H, 2.97; N, 8.70. Found (%): C, 60.55; H, 2.87; N, 8.79. IR (KBr, cm-1): 3065s, 1712s, 1560s, 1490s, 1463w, 1397s, 1361s, 1339w, 1232w, 1139m, 1076s, 1007w, 881s, 827s, 750s, 679m, 639w, 484w.
Zn (NO3)2·6H2O (0.0595 g, 0.2 mmol), DPPZ (0.0565 g, 0.2 mmol), 2, 4′-H2bpdc (0.0484 g, 0.2 mmol) and NaOH (0.016 g, 0.40 mmol) were dissolved in distilled water (15 mL), and the resulting solution was stirred for about 1 h at room temperature, sealed in a 25 mL Teflon-lined stainless- steel autoclave and heated at 433 K for 3 d under autogenous pressure. Upon cooling and opening the bomb, yellow block crystals of 2 were collected with a yield of 29% (based on 2, 4′- H2bpdc) by filtration and washed with water and ethanol for several times. Anal. Calcd. (%) for 2: C, 65.14; H, 3.57; N, 6.61. Found (%): C, 64.30; H, 3.76; N, 7.91. IR (KBr, cm-1): 3061s, 1608s, 1540s, 1496s, 1448w, 1404s, 1360s, 1240w, 1130m, 1076s, 1006w, 869s, 824s, 759s, 673m, 618w.
2.3 Structure determination
Crystallographic data of the two coordination complexes were collected at 293(2) K on a Bruker- AXS Smart CCD diffractometer equipped with a graphite-monochromatic MoKa radiation (λ = 0.71073 Å) by using an ω scan mode in the ranges of (1.72≤θ≤26.01º) (for 1) and (1.64≤θ≤26.06º) (for 2). The structures of 1 and 2 were solved by direct methods with SHELXS-97 program[19] and refined by SHELXL-97[20] using full-matrix leastsquares techniques on F2. The solvent molecules in complex 1 were highly disordered and weren’t refined anisotropically. All other non-hydrogen atoms were refined anisotropically and hydrogen atoms isotro- pically. All H atoms on C atoms were positioned geometrically (C-H = 0.93 Å) and refined as riding, with Uiso (H) = 1.2Ueq (C). Further crystallographic data and experimental details for structural analyses of 1 and 2 are summarized in Table 1.
Compound 1 2 Formula C64H38Cd2N8O9 C46H30ZnN4O9 Formula mass 1287.82 848.11 Crystal system Monoclinic Triclinic Space group C2/c P1 Crystal size (mm) 0.497 × 0.304 × 0.205 0.462 × 0.213 × 0.197 a (Å) 20.3990(18) 10.4333(13) b (Å) 23.687(2) 12.4566(16) c (Å) 13.6036(12) 15.0353(19) α (°) 90 85.404(2) β (°) 120.1890(10) 85.798(2) γ (°) 90 89.185(2) V (Å3) 5681.7(9) 1942.5(4) Z 4 2 M (mm-1) 0.814 0.698 Goodness-of-fit on F2 1.048 1.056 Reflns collected/unique 14375/5174 9974/6969 Dcalc (Mg m-3) 1.506 1.45 θ range (°) 1.75 to 25.34 1.64 to 25.35 R (I > 2σ(I)) 0.0486, 0.1319 0.0703, 0.1713 R (all data) 0.0805, 0.1517 0.1176, 0.2156 Table 1. Crystallographic Data for Complexes 1 and 23 RESULTS AND DISCUSSION
3.1 Description of the crystal structures
3.2 XRD analysis and thermogravimetry analysis (TGA)
As shown in Fig. 6, the good accordance of the experimental XRD patterns with the simulated patterns indicates phase purities of complexes 1 and 2, respectively.
The thermal stabilities of complexes 1 and 2 were investigated by using TG analyzer under atmospheric conditions from 40 to 800 ℃. As shown in Fig. 7, the TG curve of 1 shows three main steps of weight loss in the temperature range of 40~800 ℃. The first weight loss occurred between 93 and 107 ℃ due to the departure of lattice water molecules by 1.41% (calcd. 1.40%). Then the second one corresponding to the release of 2, 4′-bpdc ligand is 37.33% (calcd. 37.28 %) from 328 to 428 ℃. The third step (43.87 %) from 428 to 601 ℃ is attributed to the removal of DPPZ ligand (calcd. 43.84 %). The TG curve of 2 also exhibits three steps of weight loss in the temperature range of 40~800 ℃. The first weight loss corresponding to the release of lattice water molecules is 2.23% (calcd. 2.12%) from 89 to 120 ℃. The second one of 55.92% is in the range of 315~431° C, assigned to the loss of organic ligands 2, 4′-Hbpdc (calcd. 56.85%). The third weight loss of 33.36% is ascribed to the decomposition of DPPZ ligand (calcd. 33.29%) from 431 to 120 ℃.
3.3 Photoluminescent properties
The photoluminescent properties of 1 and 2 are studied in the solid state at room temperature. As shown in Fig. 8, complexes 1 and 2 both exhibit green photoluminescence with an emission maximum at ca. 532 and 540 nm upon excitation at 365 nm. The free 2, 4′-H2bpdc and DPPZ ligands exhibit the maximum emission at 354[21] and 444 nm[22], respectively. The emission spectra of 1 and 2 are similar to the DPPZ ligand, which may probably be assigned to the intraligand (n→π* or π→π*) transfer[23].
3.1.2 Structure description of 2
The structure of complex 2 features a mononuclear Zn (II) cluster unit. As shown in Fig. 4, the asymmetric unit of 2 contains one ZnII ion, one DPPZ ligand, two 2, 4′-Hbpdc ligands and one uncoordinated water molecule. ZnII adopts a distorted octahedral geometry coordinated by two N atoms (N (1) and N (2)) from one DPPZ ligand and four O atoms (O (1), O (2), O (5) and O (6)) from two different 2, 4′-Hbpdc ligands. One of the carboxyl groups of each 2, 4′-Hbpdc is deprotonated and coordinates to the central ZnII ions in a bidentate chelating mode, while the other is unprotonated (Scheme 1b). Simultaneously, the neighboring mononuclear units are ulteriorly stacked to furnish a 2D supramolecular layered structure (Fig. 5) via π-π interactions between DPPZ ligands (centroid-tocentroid distance ca. 3.589(3) Å). Further, the O (4)- H (4)…O (6) hydrogen bond of the carboxylic groups of 2, 4′-Hbpdc is also present within the 2D supramolecular structure.
3.1.1 Structure description of 1
Single-crystal X-ray diffraction analysis reveals that the coordination complex [Cd (2, 4′- bpdc)(DPPZ)]2n·nH2O crystallizes in C2/c space group, which is a 1D chain-like structure along the a axis. The asymmetric unit of 1 consists of one CdII ion, one DPPZ ligand, two 2, 4′-bpdc ligands and one half-occupied uncoordinated water molecule. As shown in Fig. 1, each CdII ion adopts a seriously distorted octahedral geometry coordinated by two nitrogen atoms (N (1) and N (2)) from one DPPZ ligand and four carboxylate oxygen atoms (O (1), O (2), O (3) and O (4)) from two different 2, 4′-bpdc ligands. The basal plane is formed by N (1), N (2), O (1) and O (3), and the axial positions are occupied by O (2) and O (4). Each fully deprotonated 2, 4′-bpdc ligand coordinates three Co atoms, and both carboxylate groups adopt μ3 fashion (Scheme 1a). Obviously, the 2, 4′-bpdc dianion serves as a spacer to connect adjacent metal centers into a 1D chain-like configuration, with the shortest Cd…Cd distance of 4.121 Å (Fig. 2). Interestingly, the DPPZ ligands from the chains are well-matched to furnish strong π-π stacking interactions between the neighboring chains with the centroid-to-centroid distances of 3.457(3), 3.503(7) and 3.441(5) Å, generating a 3D supramolecular structure (Fig. 3).
4 CONCLUSION
In summary, two crystallographically different complexes, namely [Cd (2, 4′-bpdc)(DPPZ)]2n·nH2O (1) and [Zn (2, 4′-Hbpdc)2(DPPZ)]·H2O (2), based on mixed ligands 2, 4′-H2bpdc and DPPZ ligands were obtained under hydrothermal conditions. The results of this study demonstrate that complexes 1 and 2 display 1D chains and isolated mononuclear units, which are further connected by weak non-covalent interactions (π-π and weak hydrogen bonding interactions), generating 3D and 2D supramolecular structures, respectively. Weak non-covalent interactions play an important role in the formation of final constructions. In addition, thermal stabilities and photoluminescence properties of these two complexes were studied in the solid state at room temperature.
Complex 1 Bond Dist. Bond Dist. Bond Dist. Cd(1)-N(1) 2.390(5) Cd(1)-N(2) 2.373(4) Cd(1)-O(1) 2.529(4) Cd(1)-O(2) 2.262(4) Cd(1)-O(3) 2.326(4) Cd(1)-O(4) 2.237(4) Angle (°) Angle (°) Angle (°) O(4)-Cd(1)-O(2) 142.85(15) O(4)-Cd(1)-O(3) 104.70(14) O(2)-Cd(1)-O(3) 82.84(14) O(4)-Cd(1)-N(2) 90.62(14) O(2)-Cd(1)-N(2) 126.52(16) O(3)-Cd(1)-N(2) 81.43(14) O(4)-Cd(1)-N(1) 90.46(15) O(2)-Cd(1)-N(1) 102.31(16) O(3)-Cd(1)-N(1) 147.57(17) N(2)-Cd(1)-N(1) 69.71(17) O(4)-Cd(1)-O(1) 95.27(15) O(2)-Cd(1)-O(1) 53.55(17) O(3)-Cd(1)-O(1) 124.37(18) N(2)-Cd(1)-O(1) 150.5(2) N(1)-Cd(1)-O(1) 81.4(2) Complex 2 Bond Dist. Bond Dist. Bond Dist. Zn(1)-N(1) 2.131(5) Zn(1)-N(2) 2.091(5) Zn(1)-O(1) 2.158(4) Zn(1)-O(2) 2.152(4) Zn(1)-O(5) 2.231(4) Zn(1)-O(6) 2.153(4) Angle (°) Angle (°) Angle (°) N(2)-Zn(1)-N(1) 78.30(17) N(2)-Zn(1)-O(2) 156.74(17) N(1)-Zn(1)-O(2) 101.67(17) N(1)-Zn(1)-O(6) 94.42(17) N(2)-Zn(1)-O(6) 107.57(17) O(2)-Zn(1)-O(6) 96.65(16) N(2)-Zn(1)-O(1) 97.73(16) N(1)-Zn(1)-O(1) 117.03(18) O(2)-Zn(1)-O(1) 61.19(15) O(6)-Zn(1)-O(1) 143.16(16) N(2)-Zn(1)-O(5) 90.26(16) N(1)-Zn(1)-O(5) 146.79(17) O(2)-Zn(1)-O(5) 100.81(15) O(6)-Zn(1)-O(5) 59.20(15) O(1)-Zn(1)-O(5) 95.21(16) Table 2. Selected Bond Lengths (Å ) and Bond Angles (°) for 1 and 2 -
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Table 1. Crystallographic Data for Complexes 1 and 2
Compound 1 2 Formula C64H38Cd2N8O9 C46H30ZnN4O9 Formula mass 1287.82 848.11 Crystal system Monoclinic Triclinic Space group C2/c P1 Crystal size (mm) 0.497 × 0.304 × 0.205 0.462 × 0.213 × 0.197 a (Å) 20.3990(18) 10.4333(13) b (Å) 23.687(2) 12.4566(16) c (Å) 13.6036(12) 15.0353(19) α (°) 90 85.404(2) β (°) 120.1890(10) 85.798(2) γ (°) 90 89.185(2) V (Å3) 5681.7(9) 1942.5(4) Z 4 2 M (mm-1) 0.814 0.698 Goodness-of-fit on F2 1.048 1.056 Reflns collected/unique 14375/5174 9974/6969 Dcalc (Mg m-3) 1.506 1.45 θ range (°) 1.75 to 25.34 1.64 to 25.35 R (I > 2σ(I)) 0.0486, 0.1319 0.0703, 0.1713 R (all data) 0.0805, 0.1517 0.1176, 0.2156 Table 2. Selected Bond Lengths (Å ) and Bond Angles (°) for 1 and 2
Complex 1 Bond Dist. Bond Dist. Bond Dist. Cd(1)-N(1) 2.390(5) Cd(1)-N(2) 2.373(4) Cd(1)-O(1) 2.529(4) Cd(1)-O(2) 2.262(4) Cd(1)-O(3) 2.326(4) Cd(1)-O(4) 2.237(4) Angle (°) Angle (°) Angle (°) O(4)-Cd(1)-O(2) 142.85(15) O(4)-Cd(1)-O(3) 104.70(14) O(2)-Cd(1)-O(3) 82.84(14) O(4)-Cd(1)-N(2) 90.62(14) O(2)-Cd(1)-N(2) 126.52(16) O(3)-Cd(1)-N(2) 81.43(14) O(4)-Cd(1)-N(1) 90.46(15) O(2)-Cd(1)-N(1) 102.31(16) O(3)-Cd(1)-N(1) 147.57(17) N(2)-Cd(1)-N(1) 69.71(17) O(4)-Cd(1)-O(1) 95.27(15) O(2)-Cd(1)-O(1) 53.55(17) O(3)-Cd(1)-O(1) 124.37(18) N(2)-Cd(1)-O(1) 150.5(2) N(1)-Cd(1)-O(1) 81.4(2) Complex 2 Bond Dist. Bond Dist. Bond Dist. Zn(1)-N(1) 2.131(5) Zn(1)-N(2) 2.091(5) Zn(1)-O(1) 2.158(4) Zn(1)-O(2) 2.152(4) Zn(1)-O(5) 2.231(4) Zn(1)-O(6) 2.153(4) Angle (°) Angle (°) Angle (°) N(2)-Zn(1)-N(1) 78.30(17) N(2)-Zn(1)-O(2) 156.74(17) N(1)-Zn(1)-O(2) 101.67(17) N(1)-Zn(1)-O(6) 94.42(17) N(2)-Zn(1)-O(6) 107.57(17) O(2)-Zn(1)-O(6) 96.65(16) N(2)-Zn(1)-O(1) 97.73(16) N(1)-Zn(1)-O(1) 117.03(18) O(2)-Zn(1)-O(1) 61.19(15) O(6)-Zn(1)-O(1) 143.16(16) N(2)-Zn(1)-O(5) 90.26(16) N(1)-Zn(1)-O(5) 146.79(17) O(2)-Zn(1)-O(5) 100.81(15) O(6)-Zn(1)-O(5) 59.20(15) O(1)-Zn(1)-O(5) 95.21(16) -

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